HCID 13518417, compound → 2H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-

HRID 2292029Notes

Reaction equation

HRID 2292029 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:22])[CH2:5][S:6][C:7]=1[CH:8]1[CH:13]=[CH:12][N:11](C(OCC(Cl)(Cl)Cl)=O)[CH:10]=[CH:9]1.C(Cl)(Cl)Cl.CO>C(O)=O.[Zn]>[CH3:1][C:2]1[NH:3][C:4](=[O:22])[CH2:5][S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 13518417HCID 13518417, compoundHCID 21584188Chloroform methanol

Product 1

HCID 30625322H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-Yield 37.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 284Formic AcidSolvent

Procedure

Zinc powder (1.7 g) was added to a solution of 5-methyl-6-[1-(2,2,2-trichloroethoxycarbonyl)-1,4-dihydro-4-pyridinyl]-2H-1,4-thiazin-3(4H)-one (1g) in formic acid (14 ml) and the mixture was stirred at ambient temperature for 3 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in water (30 ml), was adjusted to pH 7.0 by 1N aqueous sodium hydroxide, was extracted with chloroform and was dried over magnesium sulfate. Chloroform was removed and the residue was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 (supplied by Merck & Co. Inc., U.S.A.), 20×20 cm, thickness=1 mm, developing solvent; chloroform/methanol=20:1] to give the titled compound (0.2 g, yield 37.1%) as pale yellow plates. The physiocochemical properties were as described above.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in water (30 ml)
  4. extractionwas extracted with chloroform
  5. dry with materialwas dried over magnesium sulfate
  6. customChloroform was removed
  7. customthe residue was purified by the preparative thin layer chromatography [Merck TLC plate, silica gel 60F254 (supplied by Merck & Co. Inc., U.S.A.), 20×20 cm

Sources & evidence

ORD record
ord-2fa0a3eeaf2d45cfb80677ca47177c8c
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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